Newly synthesized peripherally octa-substituted zinc phthalocyanines carrying halogen terminated phenoxy-phenoxy moiety: comparative photochemical and photophysical features

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Kirbac E., ERDOĞMUŞ A.

TURKISH JOURNAL OF CHEMISTRY, vol.44, no.6, pp.1556-1577, 2020 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 44 Issue: 6
  • Publication Date: 2020
  • Doi Number: 10.3906/kim-2007-56
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.1556-1577
  • Keywords: Photochemistry, photophysics, zinc phthalocyanine, octa-substituted, halogen substitution, QUANTUM YIELDS, PHOTOSENSITIZERS, DERIVATIVES, SOLVENT, CHLORO
  • Yıldız Technical University Affiliated: Yes


This study reports the 3 new phthalonitrile derivatives, namely 4, 5 Bis-[4-(4-bromophenoxy) phenoxy]phthalonitrile (1), 4,5 Bis-[4-(4-chlorophenoxy) phenoxy]phthalonitrile (2), and 4, 5 Bis[4-(4-fluorophenoxy) phenoxy]phthalonitrile (3). Their octa-substituted zinc phthalocyanines (4, 5, 6) are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods, such as UV-Vis, (HNMR)-H-1, FT-IR spectroscopy, as well as mass spectraand elemental analysis. To show photosynthesizer's potential, emission (F-F), singlet oxygen (O-1(2)), and photodegradation quantum yields (Phi(Delta), Phi(d)) of octa-peripherally phthalocyanines (Pcs) were performed in the solutions, such as biocompatible solvent UMW (dimethyl sulfoxide) as well as DWI (dimethylformamide) and THE (tetrahydrofuran). Solvent and octa-peripherally binding effect of the halogen (Br, Cl, F) terminated phenoxy-phenoxy groups on phthalocyanine rings for photophysicochemical properties (4, 5, and 6) were compared with the tetra-peripherally and tetra nonperipherally substituted derivatives. The new dyes (4 to 6) may be evaluated in photodynamic therapy (PDT) of cancer as photosensitizers due to efficient O-1(2) from 0.55 to 0.75.